Colorado Man’s Winning Recession Recovery Plan: Copywriting

The words case study over image of hand on laptop keyboard

Real estate was supposed to be Mike Connolly’s ticket to financial freedom. But instead, it left him buried in debt.

The turning point came on a cold, January morning in 2009.

“My accountant informed me we were $600,000 in the hole and bleeding $35,000 every month,” Mike said. “Real estate sales had fallen off a cliff. With no money coming in and debt piling up, bankruptcy seemed the only way out. I’d gone from being worth a couple million to less than a panhandler.”

Yet there was no time to sit back and regroup. Mike had bills to pay and a special needs son at home to support. He knew one thing though: His next career would entail less “windshield time” and more family time.

A New Gig: Copywriting


Mike Connolly

A few years back, Mike had left a successful, 20-year career in sales to pursue his dream of owning a business. Now with the business in ashes, he had to start over — from scratch.

Fortunately, the seeds of Mike’s next career — copywriting — had been planted long ago; he just didn’t know it. In his teens and 20s, as leader of a band, Mike had penned copy to land gigs and bring in fans — and did quite well at it.

“I was good at hustling gigs,” he says. “Promoting the band with flyers, news stories and whatnot was just part of the drill … I had no idea there was this profession called ‘copywriting.’”


Mike with Chamber of Commerce buddies at a networking event in Eldorado Springs

Also piquing his interest, Mike had met a copywriter where he lives in Boulder, Colorado. “He was building a beautiful house in an expensive part of town, clearly making really good money working from home,” he says. “I was fascinated.”

But how could Mike go from zero to a copywriting career that paid the bills?

Mike’s Disaster Recovery Plan

Enter Mike’s “2009 Disaster Recovery Plan,” featuring copywriting as the foundation. Over the course of a few years, Mike steadily advanced his career, putting every extra penny into learning the craft. He began with programs from legendary copywriter, Dan Kennedy.

In his studies, Mike had also heard a few mentions of AWAI. After listening to a talk by Mark Ford, one of the founders of AWAI, he decided to take a closer look at what the organization offered.

“Mark’s book, Seven Years to Seven Figures, was especially meaningful to me at the time, and still is,” he says. “I figured, if he was involved in AWAI, there must be something to it.”

When Mike checked out AWAI, he found what he’d been looking for — comprehensive copywriting instruction from some of the top names in the industry.

Mike soon joined AWAI’s Circle of Success (COS), giving him lifetime access to all AWAI programs.

COS delivered the just-in-time training Mike needed. When he wanted to learn about website optimization, AWAI covered it. The same went for sales letters, email copy, pricing strategy, and more. Steadily, he filled in the gaps in his knowledge — and his income. He also credits AWAI with helping him learn to write fast, yet effectively.

When the opportunity arose, Mike took a gig running marketing for a friend, where he gained on-the-job experience writing a high volume of emails and other copy, while continuing to study copywriting on the side.

Networking Pays Off

Despite being a longtime salesman, Mike had much to learn about how to market his copywriting business. “Gee, someone doesn’t just give you leads,” he says tongue-in-cheek. “It’s one thing to be a great copywriter, but another to make it happen from scratch, to bring business in. It was pretty intense for a while.”


Mike making new friends at a local Chamber of Commerce event

Mike found his favorite method of marketing: networking. That’s how he picked up early jobs from some of the top names in the industry. One of the first came from Robert Skrob, founder of the Information Marketing Association, an organization Mike had joined. Robert tapped Mike for the copy for an entire campaign, including landing pages, web copy, emails, postcards, and more. “That project was a godsend, a first foot in the door,” he says.

Twice, Mike has headed to Florida for AWAI’s FastTrack to Copywriting Success Bootcamp and Job Fair, an annual event that brings together hundreds of copywriters, instructors, and clients looking for writers. There, a designer friend introduced Mike to another top copywriter, David Deutsch. Conversations soon led to a project with David, allowing Mike to learn from one of the best.

“Working with David was amazing. I’d give the piece my best shot, then he’d blow my mind with his bolt-from-the-blue, dead-on ideas,” he says.

While in the marketing job, Mike had learned to use Infusionsoft software — knowledge he wisely decided to leverage. By becoming an Infusionsoft consultant, Mike immediately joined a community of thousands of small- to mid-size business owners that needed help with both the software and copywriting. Mike could craft the copy for entire campaigns that the software would execute, and advise clients on the ins and outs of doing so.


Mike with a client at ICON, the annual Infusionsoft user conference

Having made himself a valued part of the Infusionsoft community, the company has often hired him to write copy for their “Implementation Accelerators.” Small business owners from around the world attend these hands-on workshops where Mike and a handful of other creative professionals help them build their automated marketing campaigns. On occasion, these business owners, in turn, have retained Mike for their ongoing copywriting needs. Through that and other marketing efforts, he maintains a full calendar with a variety of projects for coaches, consultants, and professional service providers.

Next Target: $250,000

Today, Mike has progressed well along on his recovery plan and expects to crest six-figures in income this year. That’s with just three days a week dedicated to client projects, with the rest of the week for administration and marketing.

He even fits in yoga and visualization first thing in the morning, and swimming most afternoons. Moreover, he has the flexibility to help his son during the workday, if needed.

Mike’s next target: $250,000 annually, a goal he fully expects to reach given his dedication.

“In terms of the big money proof, I’m still working toward that grand slam sales letter that puts me clearly on the ‘A-list.’ But there’ve been so many smaller instances of clients loving what I’ve done for them. And videos I’ve scripted that remain on website front pages — evidence of their effectiveness — for years.”

“My copywriting career has been like a snowball, gathering momentum and mass as it rolls to where I am now — close to six-figures,” he says. “AWAI has been essential in helping me really hone my chops as a communicator and serves as a wellspring of ideas.”


“Cruisin’ for Veggies” at the Farmer’s Market — Mike’s Saturday morning ritual

“My favorite part of this copywriting lifestyle is no limits on income potential, or how I use my time, or where and with whom I work.”

Mike’s Tips for Copywriters

  • Network in communities — Mike found peers and clients through AWAI and especially Circle of Success, Infusionsoft groups, and the Information Marketing Association.
  • Pay yourself first — Mike writes copy for his own business first each day, and then works on client projects. He also dedicates Fridays to his own marketing.
  • Develop an effective daily discipline and stick with it.
  • Take imperfect projects — Especially early on, take projects even if they’re not exactly what you want to do. You learn something on every project.
  • Take risks — “Learn all you can, but don’t be afraid to fail,” he says. “As the great copywriter Jim Rutz said, ‘You either win or learn.’”

What help or guidance do you need to move your freelance writing career forward like Mike? Let us know in the comments below how we can help.

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Published: November 1, 2017

2 Responses to “Colorado Man’s Winning Recession Recovery Plan: Copywriting”

  1. Hello I am Clark and I am from South Africa 🇿🇦 can I also learn this skill if I leave over seas

    Guest (Clark Baloyi)

  2. Congrats to Mike! I lived in Boulder, CO. For almost 50 years and I know how hard the Great Recession was for my friend in real estate. I was a teacher for 30 years and have always been interested in writing but know nothing about copywriting! I wish I could read some of the copywriting pieces Mike has written. WR

    Guest (Martha Beals)


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